(+/-)-N-benzoyl-α-vinylalaninol | 140867-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-N-benzoyl-α-vinylalaninol
• 英文别名: N-(1-hydroxy-2-methylbut-3-en-2-yl)benzamide
• CAS: 140867-28-3
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: AVWJQLUGXWRZQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-N-benzoyl-α-vinylalaninol 在 氢氧化钾 、 硫酸 、 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 82.5h， 生成 (1R*,2R*,3S*,6S*,7S*,8S*)-6-amino-6-methyl-1,2,8-trichloro-3,9,9-trimethoxy-4-oxatricyclo<5.2.1.0^3,8>decane
  参考文献：
  名称：

  A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid

  摘要：

  Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model alpha-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal reductive amination of an alpha-keto acid via a thermal rearrangement. Diastereomer 10b undergoes the rearrangement more readily than diastereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.

  DOI：

  10.1016/s0040-4020(01)88730-5
• 作为产物：
  描述：

  (+/-)-N-benzoyl-α-vinylalanine methyl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 19.0h， 以87%的产率得到(+/-)-N-benzoyl-α-vinylalaninol
  参考文献：
  名称：

  A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid

  摘要：

  Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model alpha-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal reductive amination of an alpha-keto acid via a thermal rearrangement. Diastereomer 10b undergoes the rearrangement more readily than diastereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.

  DOI：

  10.1016/s0040-4020(01)88730-5

文献信息

• Enantiomerically enriched α-vinyl amino acids via lipase-mediated “reverse transesterification”
  作者：David B. Berkowitz、James A. Pumphrey、Quanrong Shen

  DOI：10.1016/s0040-4039(00)78486-3

  日期：1994.11

  Reduction of protected alpha-vinyl amino acids produces ''neopentyl'' alcohols that may be enriched in the L-antipode by lipase-mediated acylation with vinyl acetate. Subsequent deacetylation, oxidation and hydrolysis yields enantiomerically enriched L-alpha-vinyl amino acids.
• A new retro-aza-ene reaction: formal reductive amination of an α-keto acid to an α-amino acid
  作者：David B. Berkowitz、W. Bernd Schweizer

  DOI：10.1016/s0040-4020(01)88730-5

  日期：1992.2

  Two diastereomeric reductive amination reagents, 1a and 1b, were synthesized. Each reagent was condensed with ethyl pyruvate as a model alpha-keto acid. Flash vacuum pyrolysis of the pyruvate adducts, 10a and 10b, results in cheleotropic elimination of CO, followed by a new type of retro-aza-ene reaction. A molecule of benzene and a protected alanine derivative, 11, are produced in the retro-ene reaction. This sequence constitutes the first formal reductive amination of an alpha-keto acid via a thermal rearrangement. Diastereomer 10b undergoes the rearrangement more readily than diastereomer 10a, indicating that an exo transition state is preferred over an endo transition state for this particular retro-aza-ene reaction.